# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2339642'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 F12 Fe N12 P2'
_chemical_formula_weight         774.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5010(6)
_cell_length_b                   16.7642(14)
_cell_length_c                   11.2100(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.792(3)
_cell_angle_gamma                90
_cell_volume                     1406.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8499
_cell_measurement_theta_min      2.189
_cell_measurement_theta_max      27.163

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.769
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3106
_exptl_absorpt_correction_T_max  0.4302
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1094 (selected reflections only, before parameter refinement)
 R(int) =  0.0657 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20477
_diffrn_reflns_av_unetI/netI     0.0933
_diffrn_reflns_av_R_equivalents  0.1443
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.189
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3058
_reflns_number_gt                2243
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+5.1772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.500000 0.500000 1.000000 0.0118(2) Uani 1 2 d S . P . .
N1 N 0.6565(5) 0.59159(19) 0.9759(3) 0.0134(7) Uani 1 1 d . . . . .
N2 N 0.7022(5) 0.60766(19) 0.8625(3) 0.0142(7) Uani 1 1 d . . . . .
N3 N 0.6455(5) 0.43932(19) 0.8925(3) 0.0140(7) Uani 1 1 d . . . . .
N4 N 0.6933(5) 0.47582(19) 0.7905(3) 0.0152(8) Uani 1 1 d . . . . .
N5 N 0.3543(5) 0.53714(19) 0.8583(3) 0.0144(7) Uani 1 1 d . . . . .
N6 N 0.4410(5) 0.55844(19) 0.7601(3) 0.0154(8) Uani 1 1 d . . . . .
C1 C 0.7317(6) 0.6490(2) 1.0435(4) 0.0181(9) Uani 1 1 d . . . . .
H1 H 0.723089 0.653491 1.127379 0.022 Uiso 1 1 calc R U . . .
C2 C 0.8250(6) 0.7019(3) 0.9747(4) 0.0218(10) Uani 1 1 d . . . . .
H2 H 0.889964 0.747794 1.002028 0.026 Uiso 1 1 calc R U . . .
C3 C 0.8043(6) 0.6746(2) 0.8604(4) 0.0173(9) Uani 1 1 d . . . . .
H3 H 0.852035 0.697818 0.792070 0.021 Uiso 1 1 calc R U . . .
C4 C 0.7236(6) 0.3682(2) 0.8928(4) 0.0170(9) Uani 1 1 d . . . . .
H4 H 0.713129 0.328859 0.952977 0.020 Uiso 1 1 calc R U . . .
C5 C 0.8235(6) 0.3590(2) 0.7925(4) 0.0193(9) Uani 1 1 d . . . . .
H5 H 0.891934 0.313868 0.772463 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8020(6) 0.4286(2) 0.7295(4) 0.0175(9) Uani 1 1 d . . . . .
H6 H 0.853592 0.441403 0.656738 0.021 Uiso 1 1 calc R U . . .
C7 C 0.1834(6) 0.5508(2) 0.8292(4) 0.0186(9) Uani 1 1 d . . . . .
H7 H 0.089497 0.540950 0.880108 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1593(7) 0.5820(3) 0.7131(4) 0.0211(10) Uani 1 1 d . . . . .
H8 H 0.049719 0.597041 0.671971 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3249(7) 0.5860(2) 0.6717(4) 0.0192(9) Uani 1 1 d . . . . .
H9 H 0.354097 0.604658 0.595399 0.023 Uiso 1 1 calc R U . . .
C10 C 0.6332(6) 0.5561(2) 0.7677(4) 0.0164(9) Uani 1 1 d . . . . .
H10 H 0.677493 0.574782 0.690301 0.020 Uiso 1 1 calc R U . . .
P1 P 0.25188(17) 0.35485(6) 0.55589(10) 0.0169(3) Uani 1 1 d . . . . .
F1 F 0.4544(4) 0.3819(2) 0.5750(3) 0.0414(8) Uani 1 1 d . . . . .
F2 F 0.2093(4) 0.39503(16) 0.6793(2) 0.0316(7) Uani 1 1 d . . . . .
F3 F 0.2973(5) 0.27223(16) 0.6207(3) 0.0424(9) Uani 1 1 d . . . . .
F4 F 0.2971(4) 0.31590(15) 0.4292(2) 0.0321(8) Uani 1 1 d . . . . .
F5 F 0.0504(5) 0.3285(2) 0.5330(3) 0.0501(10) Uani 1 1 d . . . . .
F6 F 0.2067(4) 0.43722(16) 0.4867(2) 0.0317(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N1 1.962(3) 3_667 ?
Fe1 N1 1.962(3) . ?
Fe1 N3 1.962(3) . ?
Fe1 N3 1.962(3) 3_667 ?
Fe1 N5 1.969(3) 3_667 ?
Fe1 N5 1.969(3) . ?
N1 C1 1.328(5) . ?
N1 N2 1.365(5) . ?
N2 C3 1.360(5) . ?
N2 C10 1.439(5) . ?
N3 C4 1.329(5) . ?
N3 N4 1.366(5) . ?
N4 C6 1.354(5) . ?
N4 C10 1.437(5) . ?
N5 C7 1.322(6) . ?
N5 N6 1.362(5) . ?
N6 C9 1.356(6) . ?
N6 C10 1.439(6) . ?
C1 C2 1.394(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.360(6) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.400(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.368(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.403(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.356(7) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10 1.0000 . ?
P1 F5 1.579(4) . ?
P1 F1 1.586(3) . ?
P1 F2 1.590(3) . ?
P1 F3 1.590(3) . ?
P1 F6 1.609(3) . ?
P1 F4 1.619(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Fe1 N1 180.0 3_667 . ?
N1 Fe1 N3 92.34(14) 3_667 . ?
N1 Fe1 N3 87.66(14) . . ?
N1 Fe1 N3 87.66(14) 3_667 3_667 ?
N1 Fe1 N3 92.34(14) . 3_667 ?
N3 Fe1 N3 180.0 . 3_667 ?
N1 Fe1 N5 86.95(14) 3_667 3_667 ?
N1 Fe1 N5 93.05(14) . 3_667 ?
N3 Fe1 N5 91.72(15) . 3_667 ?
N3 Fe1 N5 88.28(14) 3_667 3_667 ?
N1 Fe1 N5 93.05(14) 3_667 . ?
N1 Fe1 N5 86.95(14) . . ?
N3 Fe1 N5 88.29(14) . . ?
N3 Fe1 N5 91.71(15) 3_667 . ?
N5 Fe1 N5 180.0 3_667 . ?
C1 N1 N2 105.3(3) . . ?
C1 N1 Fe1 136.4(3) . . ?
N2 N1 Fe1 118.1(3) . . ?
C3 N2 N1 110.8(3) . . ?
C3 N2 C10 131.1(4) . . ?
N1 N2 C10 118.0(3) . . ?
C4 N3 N4 105.3(3) . . ?
C4 N3 Fe1 136.6(3) . . ?
N4 N3 Fe1 118.0(2) . . ?
C6 N4 N3 111.2(3) . . ?
C6 N4 C10 130.6(4) . . ?
N3 N4 C10 118.1(3) . . ?
C7 N5 N6 105.2(3) . . ?
C7 N5 Fe1 137.0(3) . . ?
N6 N5 Fe1 117.7(3) . . ?
C9 N6 N5 111.2(4) . . ?
C9 N6 C10 130.2(4) . . ?
N5 N6 C10 118.3(3) . . ?
N1 C1 C2 110.8(4) . . ?
N1 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C3 C2 C1 106.1(4) . . ?
C3 C2 H2 127.0 . . ?
C1 C2 H2 127.0 . . ?
N2 C3 C2 106.9(4) . . ?
N2 C3 H3 126.5 . . ?
C2 C3 H3 126.5 . . ?
N3 C4 C5 110.9(4) . . ?
N3 C4 H4 124.6 . . ?
C5 C4 H4 124.6 . . ?
C6 C5 C4 105.7(4) . . ?
C6 C5 H5 127.2 . . ?
C4 C5 H5 127.2 . . ?
N4 C6 C5 107.0(4) . . ?
N4 C6 H6 126.5 . . ?
C5 C6 H6 126.5 . . ?
N5 C7 C8 110.9(4) . . ?
N5 C7 H7 124.6 . . ?
C8 C7 H7 124.6 . . ?
C9 C8 C7 105.7(4) . . ?
C9 C8 H8 127.1 . . ?
C7 C8 H8 127.1 . . ?
N6 C9 C8 106.9(4) . . ?
N6 C9 H9 126.5 . . ?
C8 C9 H9 126.5 . . ?
N4 C10 N2 109.8(3) . . ?
N4 C10 N6 109.7(3) . . ?
N2 C10 N6 109.7(3) . . ?
N4 C10 H10 109.2 . . ?
N2 C10 H10 109.2 . . ?
N6 C10 H10 109.2 . . ?
F5 P1 F1 178.37(19) . . ?
F5 P1 F2 90.84(19) . . ?
F1 P1 F2 90.43(18) . . ?
F5 P1 F3 90.3(2) . . ?
F1 P1 F3 90.8(2) . . ?
F2 P1 F3 91.20(15) . . ?
F5 P1 F6 89.60(19) . . ?
F1 P1 F6 89.36(18) . . ?
F2 P1 F6 90.43(15) . . ?
F3 P1 F6 178.37(16) . . ?
F5 P1 F4 89.90(19) . . ?
F1 P1 F4 88.82(18) . . ?
F2 P1 F4 178.66(16) . . ?
F3 P1 F4 89.92(15) . . ?
F6 P1 F4 88.46(14) . . ?

_refine_diff_density_max         0.968
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.141


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tpmibu
_database_code_depnum_ccdc_archive 'CCDC 2339643'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N6 O2'
_chemical_formula_weight         432.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0977(7)
_cell_length_b                   8.4764(5)
_cell_length_c                   20.6292(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.579(2)
_cell_angle_gamma                90
_cell_volume                     2283.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9459
_cell_measurement_theta_min      2.403
_cell_measurement_theta_max      33.173

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5975
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1788 (selected reflections only, before parameter refinement)
 R(int) =  0.0643 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32182
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4906
_reflns_number_gt                4532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+1.4610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4906
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.64987(9) 0.62735(14) 0.56813(6) 0.0224(3) Uani 1 1 d . . . . .
N2 N 0.70006(13) 0.70256(17) 0.52197(7) 0.0392(4) Uani 1 1 d . . . . .
N3 N 0.60944(9) 0.85829(14) 0.62486(6) 0.0214(3) Uani 1 1 d . . . . .
N4 N 0.63513(10) 0.96544(15) 0.67240(6) 0.0267(3) Uani 1 1 d . . . . .
N5 N 0.58762(9) 0.60611(14) 0.67207(6) 0.0217(3) Uani 1 1 d . . . . .
N6 N 0.48654(10) 0.59225(16) 0.65287(6) 0.0280(3) Uani 1 1 d . . . . .
O1 O 0.95816(9) 0.65123(14) 0.65852(6) 0.0351(3) Uani 1 1 d . . . . .
O2 O 0.80063(8) 0.55433(12) 0.66350(5) 0.0272(2) Uani 1 1 d . . . . .
C1 C 0.65099(11) 0.69994(16) 0.63210(7) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.62761(12) 0.47637(19) 0.55137(8) 0.0291(3) Uani 1 1 d . . . . .
H2 H 0.594819 0.400753 0.576629 0.035 Uiso 1 1 calc R U . . .
C3 C 0.66123(13) 0.4535(2) 0.49128(8) 0.0345(4) Uani 1 1 d . . . . .
H3 H 0.655596 0.360379 0.465622 0.041 Uiso 1 1 calc R U . . .
C4 C 0.70554(15) 0.5960(2) 0.47570(8) 0.0397(4) Uani 1 1 d . . . . .
H4 H 0.736312 0.614597 0.436234 0.048 Uiso 1 1 calc R U . . .
C5 C 0.53356(12) 0.91083(19) 0.58215(8) 0.0290(3) Uani 1 1 d . . . . .
H5 H 0.502363 0.854754 0.545925 0.035 Uiso 1 1 calc R U . . .
C6 C 0.51035(12) 1.05966(19) 0.60097(8) 0.0309(3) Uani 1 1 d . . . . .
H6 H 0.460934 1.129368 0.580524 0.037 Uiso 1 1 calc R U . . .
C7 C 0.57504(13) 1.08740(19) 0.65689(8) 0.0306(3) Uani 1 1 d . . . . .
H7 H 0.575841 1.182886 0.681040 0.037 Uiso 1 1 calc R U . . .
C8 C 0.61385(12) 0.52545(17) 0.72789(7) 0.0247(3) Uani 1 1 d . . . . .
H8 H 0.680064 0.518865 0.750148 0.030 Uiso 1 1 calc R U . . .
C9 C 0.52640(13) 0.45581(18) 0.74567(8) 0.0307(4) Uani 1 1 d . . . . .
H9 H 0.518811 0.391334 0.782645 0.037 Uiso 1 1 calc R U . . .
C10 C 0.45034(13) 0.49997(19) 0.69763(8) 0.0306(3) Uani 1 1 d . . . . .
H10 H 0.380838 0.467626 0.697128 0.037 Uiso 1 1 calc R U . . .
C11 C 0.76121(11) 0.71150(17) 0.66203(8) 0.0248(3) Uani 1 1 d . . . . .
H11A H 0.802235 0.780374 0.635335 0.030 Uiso 1 1 calc R U . . .
H11B H 0.762965 0.755538 0.706556 0.030 Uiso 1 1 calc R U . . .
C12 C 0.90285(11) 0.53995(18) 0.66273(7) 0.0233(3) Uani 1 1 d . . . . .
C13 C 0.93440(12) 0.36892(18) 0.66841(7) 0.0254(3) Uani 1 1 d . . . . .
H13 H 0.891173 0.317024 0.700082 0.031 Uiso 1 1 calc R U . . .
C14 C 1.04540(13) 0.3565(2) 0.69521(9) 0.0376(4) Uani 1 1 d . . . . .
H14A H 1.088963 0.413313 0.666552 0.056 Uiso 1 1 calc R U . . .
H14B H 1.065738 0.245287 0.697552 0.056 Uiso 1 1 calc R U . . .
H14C H 1.053206 0.402996 0.738820 0.056 Uiso 1 1 calc R U . . .
C15 C 0.91370(11) 0.28661(17) 0.60294(7) 0.0229(3) Uani 1 1 d . . . . .
C16 C 0.96753(12) 0.32460(18) 0.54964(8) 0.0281(3) Uani 1 1 d . . . . .
H16 H 1.015608 0.408710 0.552822 0.034 Uiso 1 1 calc R U . . .
C17 C 0.95180(12) 0.24099(19) 0.49182(8) 0.0289(3) Uani 1 1 d . . . . .
H17 H 0.989389 0.268346 0.455932 0.035 Uiso 1 1 calc R U . . .
C18 C 0.88203(12) 0.11833(18) 0.48588(7) 0.0257(3) Uani 1 1 d . . . . .
C19 C 0.82667(13) 0.08329(19) 0.53892(8) 0.0297(3) Uani 1 1 d . . . . .
H19 H 0.777236 0.001075 0.535494 0.036 Uiso 1 1 calc R U . . .
C20 C 0.84255(12) 0.16635(19) 0.59649(7) 0.0274(3) Uani 1 1 d . . . . .
H20 H 0.803994 0.140341 0.632099 0.033 Uiso 1 1 calc R U . . .
C21 C 0.86456(13) 0.0231(2) 0.42404(8) 0.0328(4) Uani 1 1 d . . . . .
H21A H 0.860616 -0.089971 0.435547 0.039 Uiso 1 1 calc R U . . .
H21B H 0.924227 0.036973 0.398000 0.039 Uiso 1 1 calc R U . . .
C22 C 0.76726(12) 0.06858(19) 0.38219(7) 0.0286(3) Uani 1 1 d . . . . .
H22 H 0.709512 0.072194 0.411074 0.034 Uiso 1 1 calc R U . . .
C23 C 0.77637(14) 0.2300(2) 0.35186(9) 0.0377(4) Uani 1 1 d . . . . .
H23A H 0.830085 0.227895 0.321408 0.057 Uiso 1 1 calc R U . . .
H23B H 0.793999 0.307850 0.386040 0.057 Uiso 1 1 calc R U . . .
H23C H 0.710937 0.258671 0.328480 0.057 Uiso 1 1 calc R U . . .
C24 C 0.74152(14) -0.0556(2) 0.32996(8) 0.0381(4) Uani 1 1 d . . . . .
H24A H 0.676971 -0.027748 0.305310 0.057 Uiso 1 1 calc R U . . .
H24B H 0.734530 -0.158833 0.350536 0.057 Uiso 1 1 calc R U . . .
H24C H 0.796504 -0.060043 0.300461 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.351(2) . ?
N1 N2 1.3584(18) . ?
N1 C1 1.4551(18) . ?
N2 C4 1.321(2) . ?
N3 C5 1.3500(19) . ?
N3 N4 1.3592(17) . ?
N3 C1 1.4517(18) . ?
N4 C7 1.323(2) . ?
N5 N6 1.3564(17) . ?
N5 C8 1.3594(18) . ?
N5 C1 1.4528(18) . ?
N6 C10 1.326(2) . ?
O1 C12 1.1967(19) . ?
O2 C12 1.3457(18) . ?
O2 C11 1.4282(17) . ?
C1 C11 1.527(2) . ?
C2 C3 1.362(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.361(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.365(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.509(2) . ?
C13 C14 1.517(2) . ?
C13 C15 1.525(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.380(2) . ?
C15 C16 1.390(2) . ?
C16 C17 1.389(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(2) . ?
C18 C21 1.511(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.530(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.513(2) . ?
C22 C24 1.525(2) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N2 111.82(13) . . ?
C2 N1 C1 128.23(13) . . ?
N2 N1 C1 117.84(12) . . ?
C4 N2 N1 104.05(14) . . ?
C5 N3 N4 112.18(12) . . ?
C5 N3 C1 128.51(13) . . ?
N4 N3 C1 118.32(11) . . ?
C7 N4 N3 103.85(12) . . ?
N6 N5 C8 112.24(12) . . ?
N6 N5 C1 118.05(11) . . ?
C8 N5 C1 129.71(13) . . ?
C10 N6 N5 104.04(13) . . ?
C12 O2 C11 116.27(12) . . ?
N3 C1 N5 109.77(11) . . ?
N3 C1 N1 108.73(11) . . ?
N5 C1 N1 108.57(11) . . ?
N3 C1 C11 108.47(11) . . ?
N5 C1 C11 111.72(12) . . ?
N1 C1 C11 109.54(12) . . ?
N1 C2 C3 106.78(15) . . ?
N1 C2 H2 126.6 . . ?
C3 C2 H2 126.6 . . ?
C2 C3 C4 104.98(15) . . ?
C2 C3 H3 127.5 . . ?
C4 C3 H3 127.5 . . ?
N2 C4 C3 112.33(15) . . ?
N2 C4 H4 123.8 . . ?
C3 C4 H4 123.8 . . ?
N3 C5 C6 106.80(14) . . ?
N3 C5 H5 126.6 . . ?
C6 C5 H5 126.6 . . ?
C5 C6 C7 104.91(14) . . ?
C5 C6 H6 127.5 . . ?
C7 C6 H6 127.5 . . ?
N4 C7 C6 112.23(14) . . ?
N4 C7 H7 123.9 . . ?
C6 C7 H7 123.9 . . ?
N5 C8 C9 106.53(14) . . ?
N5 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
C8 C9 C10 105.03(14) . . ?
C8 C9 H9 127.5 . . ?
C10 C9 H9 127.5 . . ?
N6 C10 C9 112.15(15) . . ?
N6 C10 H10 123.9 . . ?
C9 C10 H10 123.9 . . ?
O2 C11 C1 106.09(11) . . ?
O2 C11 H11A 110.5 . . ?
C1 C11 H11A 110.5 . . ?
O2 C11 H11B 110.5 . . ?
C1 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
O1 C12 O2 122.55(14) . . ?
O1 C12 C13 126.81(14) . . ?
O2 C12 C13 110.64(12) . . ?
C12 C13 C14 110.07(13) . . ?
C12 C13 C15 110.03(12) . . ?
C14 C13 C15 112.85(13) . . ?
C12 C13 H13 107.9 . . ?
C14 C13 H13 107.9 . . ?
C15 C13 H13 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.42(14) . . ?
C20 C15 C13 119.61(13) . . ?
C16 C15 C13 121.92(14) . . ?
C17 C16 C15 120.74(15) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.76(14) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 118.21(14) . . ?
C17 C18 C21 122.04(15) . . ?
C19 C18 C21 119.75(15) . . ?
C20 C19 C18 120.97(15) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C15 C20 C19 120.88(14) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C18 C21 C22 113.88(13) . . ?
C18 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
C18 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C24 110.62(14) . . ?
C23 C22 C21 111.79(14) . . ?
C24 C22 C21 110.62(13) . . ?
C23 C22 H22 107.9 . . ?
C24 C22 H22 107.9 . . ?
C21 C22 H22 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044





